I take a close look a mine. If there's nothing obvious, I re-use them. Always have. Never had a problem. Go to a hardware store and buy a bag load of them for when you do need to replace them. They're pennies.
I re-use mine if there is no visible cracks or tears. You don't need a microscope to see a defect bad enough to cause a leak. I also wipe a little PTFE pipe compound aroud the plug and have never had any trouble. I keep some extra O-rings around so if one is found to be bad when doing a fluid change I don't have to make a special trip to get one.
+1 I always check them every oil change and if I see any visiable defect then it goes. Like the others have said you can buy them for hardley anything and keep about 10 on hand and replace them when they need it. Keeping it in top shape will keep peace of mind. I also check the Trany dip stick O ring also. Ride safe.
a word of caution on buying your o-rings from a harware store,make sure they are the same or suitable material compared to stock,being an industrial maintenence man I know all O-rings are not created equal. Having said that my last bike had 30k on it when I sold it and I only replaced the O-ring on the oil plug once. I have a magnifying worklight on my bench and you can see plenty good enough with that to tell if your O-ring is good or bad,anyone with good eyesight should be able to see a defect big enough to leak. As someone else said common sense is a good thing to use.